1-bromo-2-(4'-cyanobiphenyl-4-yloxy)ethane | 220615-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-2-(4'-cyanobiphenyl-4-yloxy)ethane
• 英文别名: 4-cyano-4'-(2-bromoethyloxy)-biphenyl；4'-(2-Bromoethoxy)-[1,1'-biphenyl]-4-carbonitrile；4-[4-(2-bromoethoxy)phenyl]benzonitrile
• CAS: 220615-53-2
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: MNOALRHOOBLDSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(4'-cyanobiphenyl-4-yloxy)ethane 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-((4'-cyano-(1,1'-biphenyl)-4-yl)oxy)ethyl)-N-hydroxyacetamide
  参考文献：
  名称：

  Biaryl Ether Retrohydroxamates as Potent, Long-lived, Orally Bioavailable MMP Inhibitors

  摘要：

  A novel series of biaryl ether reverse hydroxamate MMP inhibitors has been developed. These compounds are potent MMP-2 inhibitors with limited activity against MMP-1. Select members of this series exhibit excellent pharmacokinetic properties with long elimination half-lives (7 h) and high oral bioavailability (100%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00031-2
• 作为产物：
  描述：

  氰基联苯酚 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-bromo-2-(4'-cyanobiphenyl-4-yloxy)ethane
  参考文献：
  名称：

  N-Hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8

  摘要：

  The first crystallographic structure of an N-hydroxyurea inhibitor bound into the active site of a matrix metalloproteinase is reported. The ligand and three other analogues were prepared and studied as inhibitors of MMP-2, MMP-3, and MMP-8. The crystal structure of the complex with MMP-8 shows that the N-hydroxyurea, contrary to the analogous hydroxamate, binds the catalytic zinc ion in a monodentate rather than bidentate mode and with high out-of-plane distortion of the amide bonds.

  DOI：

  10.1016/j.bmcl.2005.09.057

文献信息

• High performance all-solid-state dye-sensitized solar cells based on cyanobiphenyl-functionalized imidazolium-type ionic crystals
  作者：Huizi Cao-Cen、Jie Zhao、Lihua Qiu、Dan Xu、Qing Li、Xiaojian Chen、Feng Yan

  DOI：10.1039/c2jm31551c

  日期：——

  Organic ionic crystals carrying 4-cyano-4′-hydroxybiphenyl and imidazolium units were synthesized and applied as the electrolytes for dye-sensitized solar cells (DSSCs). The fabricated all-solid-state DSSCs achieved a cell efficiency of ∼5.11% at 55 °C under the simulated air mass 1.5 solar spectrum illuminations at 100 mW cm−2 because of the enhanced light harvesting capability of the electrolyte. To further improve the cell efficiency, 1-propyl-3-methylimidazolium iodine (PMII), was added into the electrolytes as a crystal growth inhibitor. These fabricated devices showed an enhanced power conversion efficiency (PCE) of ∼6.55% at 45 °C under the simulated air mass 1.5 solar spectrum illuminations at 50 mW cm−2, and a superior long-term stability. The cyanobiphenyl-functionalized ionic crystal based electrolytes have expanded our vision to explore new types of all-solid-state electrolytes for high-efficiency DSSCs.

  合成了含有4-氰基-4'-羟基联苯和咪唑单位的有机离子晶体，并将其应用于染料敏化太阳能电池（DSSCs）的电解质。制造的全固态DSSCs在55°C下，在模拟空气质量1.5太阳光谱照射下，100 mW cm−2的条件下达到了约5.11%的电池效率，得益于电解质增强的光捕获能力。为了进一步提高电池效率，向电解质中添加了1-丙基-3-甲基咪唑碘化物（PMII）作为晶体生长抑制剂。这些制备的器件在45°C、模拟空气质量1.5太阳光谱照射下，50 mW cm−2的条件下显示出增强的功率转换效率（PCE），约为6.55%，并且具有优越的长期稳定性。功能化氰基联苯的离子晶体基电解质拓宽了我们探索新型高效全固态电解质用于DSSC的视野。
• NOVEL PDLC FILMS BASED ON A PHOTOACTIVE POLYMERIC BINDER
  作者：Alessandro Manni、Luigi Gobbi、Francesco Simoni、Markus Klapper、Wolfgang Knoll

  DOI：10.1080/15421400390221835

  日期：2003.1

  We report the synthesis and characterization of a novel polymeric material which has been used as binder in the fabrication of PDLC films. A monomer bearing a carbazolyl moiety has been copolymerized, using azobisisobutyrronitrile (AIBN) as initiator with a monomer containing a mesogenic core. PDLC films have been prepared using copolymers with different composition in the two monomers. A detailed morphological analysis has been carried out to evaluate a correlation between the copolymer composition and the PDLC film morphologies.
• Biaryl Ether Retrohydroxamates as Potent, Long-lived, Orally Bioavailable MMP Inhibitors
  作者：Michael R. Michaelides、Joseph F. Dellaria、Jane Gong、James H. Holms、Jennifer J. Bouska、Jamie Stacey、Carol K. Wada、H.Robin Heyman、Michael L. Curtin、Yan Guo、Carole L. Goodfellow、Ildiko B. Elmore、Daniel H. Albert、Terrance J. Magoc、Patrick A. Marcotte、Douglas W. Morgan、Steven K. Davidsen

  DOI：10.1016/s0960-894x(01)00031-2

  日期：2001.6

  A novel series of biaryl ether reverse hydroxamate MMP inhibitors has been developed. These compounds are potent MMP-2 inhibitors with limited activity against MMP-1. Select members of this series exhibit excellent pharmacokinetic properties with long elimination half-lives (7 h) and high oral bioavailability (100%). (C) 2001 Elsevier Science Ltd. All rights reserved.
• N-Hydroxyurea as zinc binding group in matrix metalloproteinase inhibition: Mode of binding in a complex with MMP-8
  作者：Cristina Campestre、Mariangela Agamennone、Paolo Tortorella、Serena Preziuso、Alessandro Biasone、Enrico Gavuzzo、Giorgio Pochetti、Fernando Mazza、Oliver Hiller、Harald Tschesche、Valerio Consalvi、Carlo Gallina

  DOI：10.1016/j.bmcl.2005.09.057

  日期：2006.1

  The first crystallographic structure of an N-hydroxyurea inhibitor bound into the active site of a matrix metalloproteinase is reported. The ligand and three other analogues were prepared and studied as inhibitors of MMP-2, MMP-3, and MMP-8. The crystal structure of the complex with MMP-8 shows that the N-hydroxyurea, contrary to the analogous hydroxamate, binds the catalytic zinc ion in a monodentate rather than bidentate mode and with high out-of-plane distortion of the amide bonds.